7-DEAZAGUANINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N4O
Molecular Weight	150.138
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(C=CN2)C(=O)N1

InChI

InChIKey=OLAFFPNXVJANFR-UHFFFAOYSA-N

InChI=1S/C6H6N4O/c7-6-9-4-3(1-2-8-4)5(11)10-6/h1-2H,(H4,7,8,9,10,11)

HIDE SMILES / InChI

Molecular Formula	C6H6N4O
Molecular Weight	150.138
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Direct voltammetric analysis of DNA modified with enzymatically incorporated 7-deazapurines.	2010-08-15	20704370
Crystal structure and molecular dynamics studies of human purine nucleoside phosphorylase complexed with 7-deazaguanine.	2010-03	19932753
Probing RNA conformational dynamics and heterogeneity using femtosecond time-resolved fluorescence spectroscopy.	2009-10	19362148
Portability of the GN(R)A hairpin loop motif between RNA and DNA.	2009-09-22	19681609
Introduction of cationic charge into DNA near the major groove edge of a guanine x cytosine base pair: characterization of oligodeoxynucleotides substituted with 7-aminomethyl-7-deaza-2'-deoxyguanosine.	2009-09-02	19663509
A facile synthetic approach to 7-deazaguanine nucleosides via a Boc protection strategy.	2009-06-04	19422208
Molecular recognition of a thymine bulge by a high affinity, deazaguanine-based hydrogen-bonding ligand.	2009-02-14	19322416
Generation of DNA interstrand cross-links by post-synthetic reductive amination.	2009-02-05	19132933
Formation of purine-purine mispairs by Sulfolobus solfataricus DNA polymerase IV.	2008-08-05	18616289
Systematic study of the influence of base-step parameters on the electronic coupling between base-pair dimers: comparison of A-DNA and B-DNA forms.	2008-07-31	18613656
Minisequencing with acyclonucleoside triphosphates tethered to lanthanide(III) chelates.	2008-06	18505280
Chromophore/DNA interactions: femto- to nanosecond spectroscopy, NMR structure, and electron transfer theory.	2008-01-24	18163608
Mg2+ binding and archaeosine modification stabilize the G15 C48 Levitt base pair in tRNAs.	2007-09	17652139
The distributions, mechanisms, and structures of metabolite-binding riboswitches.	2007	17997835
Nonpolar nucleobase analogs illuminate requirements for site-specific DNA cleavage by vaccinia topoisomerase.	2006-11-24	17005552
Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide incorporating 7-deazaguanine bases.	2006-11-01	16945544
Structure-activity relationship studies on the immune stimulatory effects of base-modified CpG toll-like receptor 9 agonists.	2006-09	16952134
Binding of actinomycin C1 (D) and actinomin to base-modified oligonucleotide duplexes with parallel chain orientation.	2006-06-15	16500105
Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries.	2006-05	16556935
Structure of purine-purine mispairs during misincorporation and extension by Escherichia coli DNA polymerase I.	2006-03-21	16533057
Mechanism and substrate specificity of tRNA-guanine transglycosylases (TGTs): tRNA-modifying enzymes from the three different kingdoms of life share a common catalytic mechanism.	2005-11	16206323
Recognition of guanines at a double helix-coil junction in DNA by a trinuclear copper complex.	2005-10-14	16193123
Unrestricted accessibility of short oligonucleotides to RNA.	2005-09	16120834
Detection of single base mismatches and abasic sites using phenanthridinium as an artificial DNA base and charge donor.	2005-01-07	15602596
7-deazapurin-2,6-diamine and 7-deazaguanine: synthesis and property of 7-substituted nucleosides and oligonucleotides.	2005	16248045
Synthesis of 5-aza-7-deazaguanine nucleoside derivatives as potential anti-flavivirus agents.	2005	16248011
Fluorescence properties of 2-aminopurine-cytidine-7-deazaguanine (5'-ApCdzG-3') trimer in B- and Z-DNA.	2004-02-07	14740031
DNA sequence recognition by bispyrazinonaphthalimides antitumor agents.	2003-10-14	14529286
2-Aminopurine: a probe of structural dynamics and charge transfer in DNA and DNA:RNA hybrids.	2002-11-06	12405832
DNA sequence recognition by the antitumor drug ditercalinium.	2002-07-09	12093285
Crystal structure of archaeosine tRNA-guanine transglycosylase.	2002-05-03	12054814
Dynamics and energetics of hole trapping in DNA by 7-deazaguanine.	2002-03-15	12491301
Toward electrochemical resolution of two genes on one electrode: using 7-deaza analogues of guanine and adenine to prepare PCR products with differential redox activity.	2002-01-15	11811407
On the apparently anomalous distance dependence of charge-transfer rates in 9-amino-6-chloro-2-methoxyacridine-modified DNA.	2001-10-17	11592883
Localization of Fe(2+) at an RTGR sequence within a DNA duplex explains preferential cleavage by Fe(2+) and H2O2.	2001-10-05	11580252
8-aza-7-deazaadenine and 7-deazaguanine: synthesis and properties of nucleosides and oligonucleotides with nucleobases linked at position-8.	2001-09-21	11563075
Phosphoramidites and oligonucleotides containing 7-deazapurines and pyrimidines carrying aminopropargyl side chains.	2001-09-21	11563035
The C(8)-(2'-deoxy-beta-D-ribofuranoside) of 7-deazaguanine: synthesis and base pairing of oligonucleotides with unusually linked nucleobases.	2001-05-18	11348111
Oxidation of 7-deazaguanine by one-electron and oxo-transfer oxidants: mismatch-dependent electrochemistry and selective strand scission.	2001-03-26	11261981
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.	1995-11-09	7503772

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:11:52 GMT 2025` Edited by `admin` on `Mon Mar 31 23:11:52 GMT 2025`
Record UNII	GPL8T5ZO3M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

7-DEAZAGUANINE

Common Name

English

2-AMINO-3,7-DIHYDROPYRROLO(2,3-D)PYRIMIDIN-4-ONE

Preferred Name

English

NSC-62498

Code

English

4H-PYRROLO(2,3-D)PYRIMIDIN-4-ONE, 2-AMINO-1,7-DIHYDRO-

Systematic Name

English

7H-PYRROLO(2,3-D)PYRIMIDIN-4-OL, 2-AMINO-

Systematic Name

English

Code System Code Type Description

DRUG BANK

DB02245